Why did Willy expect Biff to amount to so much more than he has?  

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Willy has the delusional idea that Biff will amount to be a success in the business world simply because he is attractive and has attained athletic success as an adolescent. In Willy's mind, a person simply needs to be well liked in order to become a success, and he genuinely believes that Biff has that specific attribute that can make him extremely wealthy. As a child, Willy neglected to instill positive character traits like dedication, honesty, and integrity into his children, and Biff has fallen short of Willy's expectations, as a thirty-four-year-old man with no steady job or income. Willy's faith in Biff's potential is strictly based off of Biff's athletic accomplishments in grade school and his physical attractiveness. Willy believes that since Biff is physically fit, handsome, and athletically talented, he can automatically attain success as an adult. Despite Biff's numerous failures as an adult, Willy still believes that his son can attain wealth and success by going into business with Happy and moving to Florida. In contrast, Biff finally accepts the reality of his situation by the end of the play and realizes that he will never live up to his father's delusional expectations.

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Willy based his expectations of Biff on Biff's "personal attractiveness."  In Willy's view of the world, personality is the key to success, and Biff's early success in life as an athlete and a leader on his sports team show Willy that Biff has what it takes to succeed, no matter what he knows.

The antithesis to Biff is Bernard.  Bernard has no personal attractiveness, but he does work hard and turns out to be a great success, arguing a case before the Supreme Court.  Willie predicted that Bernard would never amount to anything because he didn't have the "personal attractiveness" that Biff had.

 

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